


No Such Thing as Wrong

by pizza_party_in_the_tardis



Category: Supernatural
Genre: AU Alastair is still alive, Angel Castiel, Angel!Castiel, BDSM, Blood, Bondage, Demon Dean, Demon Dean Winchester, Demon!Dean, Demons, M/M, Mild torture, Original Character(s), Sadism, Taboo, dom!Dean, forcefulness, reluctance, shaming, tagging this with everything just as a warning
Language: English
Status: In-Progress
Published: 2013-07-07
Updated: 2013-07-22
Packaged: 2017-12-17 23:57:11
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 13,275
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/873374
Author URL: https://archiveofourown.org/users/pizza_party_in_the_tardis/pseuds/pizza_party_in_the_tardis
Summary: <blockquote class="userstuff">
              <p>Castiel must once again rescue Dean Winchester from Hell. After fighting his way into the pit, Castiel cannot find him anywhere. Hell’s residents are reluctant to talk to him, but he overhears gruesome rumours of a Master Torturer that goes by the name Dean. Castiel sets out to find this Torturer and comes to the horrific realization that he is too late. Dean Winchester has already become a demon.<br/>He decides he must rescue this soul, no matter its form, but when Demon Dean sees the angel, the human lust he had once felt for Cas is overwhelming. It racks his body, stronger than ever, amplified by the evil that has taken him over. His demonic impulses make him want to hurt Cas, to break the angel's innocence and since there's no such thing as <i>wrong</i> in Hell, Cas gives in.</p>
            </blockquote>





	1. The Transformation

**Author's Note:**

> I'm not sure how crazy I'm willing to get with this, but there's definitely going to be domination and sadism. Some blood!kink might find it's way in there and bondage? Hell, I'm not sure what else will end up in here, but just be warned! If any of that stuff is triggering or offensive to you, this is not the right smut for you!  
> _____________  
> 

**Summary for the Chapter:**

> Dean has been cast back into Hell and has once again become Alastair's little project.

                Alastair could see it. He could see it spark into Dean, twinkling in his eyes, reviving his posture, tugging at the corners of his mouth. A pleasurable, sadistic shiver ran up Alastair’s spine as he realized what these subtle changes meant. Dean Winchester, the cocky son of a bitch, had finally snapped. He remembered when Dean had stepped off the rack for the first time, taking the torture instruments into his own hand. Dean had had tears in his eyes. He really didn’t want to be doing this, but he couldn’t take it himself any longer. Alastair remembered how long it had taken to get Dean to that point and he relished in the satisfaction that long-awaited moment had brought him. He remembered the exact day months later when the concern and reluctance had slipped out of Dean’s expression and were replaced with a calm apathy. That was another great moment for Alastair, watching the righteous man quit caring about what he was doing to other human souls. The memory alone made Alastair lick his lips. It had been a truly satisfying day, but it was nothing compared to how he felt now. Dean’s apathy had been replaced with enjoyment, with pleasure even. Dean Winchester had been torturing other unfortunate souls for months now, but now… Now he was _finally_ starting to like it, to get pleasure and satisfaction from it, to _want_ to rip other souls apart on the rack. Alastair was so pleased with his little prodigy. The righteous man, the hunter, the demon-killer had finally become the thing he hated most. A demon.

* * *

                Dean didn’t know what had happened to him. One second his mind was numb and empty, an autonomous engine that kept him doing what he needed to do to stay alive, but the next. Oh… That was something else. He felt like he’d been struck by black lightning, a dark raw power surged through his veins. The electricity crackled through him, bringing a new vigor to every part of his body. He felt strong, alive, and keenly aware of the whip in his hand. He closed his fingers around the worn leather handle. He liked the weight of it in his hand, the sheen of the leather against his fingertips, and the way it snapped when he flicked his wrist. Yeah. He could get used to this. He turned back to the rack, drawing the whip back and cracking it down on the chest of the man tied there. He was fascinated by the red welt left after the whip drew away. He had been leaving these marks on souls for months, but he took a renewed interest in them now. And the sounds- the flash of the whip in the air, the snap as it made contact, and the man’s screams... Each sensation brought a wave of pleasure to Dean.  Each time the frayed tip of the whip met flesh, power coursed through Dean’s entire body. It was intoxicating and invigorating at the same time. He felt more alive than he had in months and he began to wonder what sensations other instruments would bring him. Before this sudden transformation, the whip had been his favorite because he could stand back from his victim and wince away from their pained expressions. But now… Dean wanted to, needed to, _see_ those expressions. He just knew each variation of a face contorted in panic and desperation and pain would be like a new flavor of his favorite food.

He stepped forward to his table of instruments, running his electrically-charged hands over the many tools laid out before him. Knives, needles, shards of glass, and all kinds of sharp and ragged items designed to inflict pain were present. Ropes and chains littered the empty spaces between weapons and Dean couldn’t pick just one. He grabbed a rusted and broken Bowie knife and a splintered piece of wood in his left hand. With a perverted, crooked grin, Dean turned back to the man on the rack. “I think I’ve been selfish lately,” he purred slowly, his tone dripping with sarcasm.  “I’ve only been doing what _I_ wanted. I think it’s time we focused on _you_.” He raised a hand to the man’s chin and cupped it forcefully. Forget weapons. Taking a soul into his own hands sent a shudder up and down his spine. Looking into the man’s wide, panicked eyes, he whispered evilly “Which one do _you_ want?” He held the two weapons up, and as he watched the man’s eyes flicker between both terrible options, the evil coursing through his veins overflowed into his eyes. Dean’s eyes were emptied of all humanity and the green color drained out of them, replaced with an inky black that burned with malice.


	2. Liars

**Summary for the Chapter:**

> Castiel has made his way into Hell and must rely on the word of demons to find Dean Winchester.

                Castiel had been in Hell for four days. Four days in this stinking, burning pit searching for Dean. Again. He was livid that Dean had been stupid enough to get himself thrown back in, but he refused to leave him there. Cas had saved him once and he could do it again, even if it was much different this time. Last time, it had just been a mission, an order from God. Now it was personal. He was rescuing Dean because he wanted to, because Dean was his friend, his best friend. That motivation made this journey more bearable, because he knew he was fighting to bring a righteous man back into the world where he belonged. It also made this journey more terrifying. Cas knew the consequences if he didn’t reach Dean in time… and he had already wasted so much of it trying to break into Hell. Cas shook the thought from his head and trudged on.    

* * *

    

                “I… I think maybe I’ve heard that name before… Maybe.  I really dunno. Please, man,” the demon whimpered out. Cas held the demon up by the neck, threatening to smite him unless he helped him find a human soul named Dean Winchester. Cas gripped tighter and the demon flinched and sputtered, “Please… I…I…” The demon looked like he was about to black out and seemed honest about not knowing, or at least as honest as a demon could be. Cas released him.

                “Tell me where you have heard this name.” Cas glared down at the crouching demon. The demon rubbed his neck and coughed.

“Gimme a second, dude.”

                Clearly this demon had been a surfer when he was a human and he hadn’t quite let go of the obnoxious lingo. Cas found this increasingly frustrating and he took a step towards the demon with his hand stretched towards his neck.

                “Come on, brah. Come on. I gotta think.” The demon sat pondering for a minute, trying to look deep in thought. “I’ve heard rumours. There’s a Dawn or a Dean or something like that, man.”

                Cas perked up . “There are many Deans. Is this a Dean Winchester?”

                “Man. I dunno. I just know I’ve heard the name around a lot. He’s like one of Alastair’s bros.”

                “Alastair? Alastair the torturer?” Cas’s eyes widened with dread. He knew Alastair had taken to Dean last time he’d been in Hell, torturing the man until he gave in and began the Apocalypse.

                “Yeah, bro. That’s the only Alastair I know ‘bout. Word is he’s got some new guy playing out all his kinks on the fresh souls. Pretty fucked up stuff, but hey. We’re demons.” The surfer demon tried to chuckle and play it off, but Cas glared at him and his laughter dwindled into silence as Cas thought about what this meant.

                He rushed towards the demon again. “Tell me where I can find Alastair. Now.”

                “Whoa, chill out, man.” The demon held up his hands in defense. “At the entrance to Hell, like the main entrance. He sets up the torture for all the newbs as they come in.”

                Cas pulled back and started to thank the demon until he remembered it was a demon. They didn’t deserve thanks of any kind. He began to walk away and the demon got up and trailed him for a few steps. “So how’d you get in here anyway, bro?” he questioned.

Cas reached an arm back without looking and pressed against the demon’s forehead. Light shone from the demon’s eyes and he fell to the ground, smited, as Cas kept on walking.

                “I am not your ‘bro.’”

* * *

 

                Cas came across many more demons on his way to Hell’s main entrance, where all souls passed through. Most of the demons attempted to capture or kill Cas, eager to turn him in to Crowley for a reward. Cas easily smited them all without a second thought. The demons that didn’t attack him weren’t eager to talk, but they weren’t looking to get smited either so they cooperated. All reported to Castiel about a new torturer called Dean.

                “One of the best we’ve ever had. “ taunted a blonde demon. “Oh yeah. Alastair turned him into a great one. Apparently the guy had a lot of trust and abandonment issues… Alastair is just magical at taking those really fucked up souls and building master torturers out of them.” She sneered at Cas as he circled her. She was dipping and diving away from his smiting touch, continually jeering at him about Dean. “I know who he is. I know who you are too, sweetheart. And don’t you think for just one damn minute that anyone down here doesn’t know the _real_ reason your feathery ass is down here to get him.” She said that last phrase with such an air of knowing that it infuriated Cas.

                “Dean is my friend. He has saved my life many times and I-“

                The demon cut him off. “Oh sweetie… Don’t kid yourself. You’re not on some holy mission this time. And after everything he’s done?” She threw her head back in feigned laughter. “You don’t owe that son of a bitch anything. You- are here- because- you _need_ him.” She paused, her eyes opening further, leering at Castiel. “Maybe… you even love him?”  He quickly looked down and away from her gaze. She clapped her hands in front of her face. “Oh-ho-ho! That’s it! Mystery solved. You’ve got yourself a big ol’ angel crush on the human you saved!”

                Cas could not believe a demon was embarrassing him like this. “Enough!” Castiel shouted.

                The blonde demon was completely unfazed by Cas’s warning. “Honey. It’s okay. This is Hell. You don’t have to worry about what we’ll think. If you wanna love a human, especially Dean Winchester, who could blame you? Those big, strong hands make your little angel heart beat faster? And what about those pretty green eyes?” She leaned in closer to his cheek to whisper in his ear. “Too bad they’re all black now.” The demon screamed out as Cas’s fingertips made contact with her forehead, sending a light out of her eyes.

                Cas immediately regretted killing her. He needed her to tell him where to find Dean, but he really couldn’t stand her jeering for a second longer. Coming from the Winchesters, teasing didn’t bother him. In fact, it made him feel like part of the family, but he would be dead before he’d allow a filthy demon to stand there and say those things to him. He wasn’t sure why it upset him so much. Demons were all liars. You couldn’t trust what they said. All they knew how to do was lie. Of course Dean wasn’t a demon... Of course he wasn’t torturing other souls... Of course Castiel didn’t have stronger-than-friends feelings for Dean… He tried to convince himself, repeating the mantra over and over as he neared Hell’s entrance. Demons. Are. _Liars._

 


	3. Brady Bunch

**Summary for the Chapter:**

> Dean's getting bored with the usual torture techniques so Alistair suggests something new for the rack's current victim, a family man.

                 “Hahaha! You think that I care? That- That is really just, oh, I don’t know. _Precious?”_ Dean rolled his eyes. “Alastair! You gotta start sending me some better souls.” He yelled to the sidelines where his teacher was watching, a proud smirk stretched across his face.” These ones are boring. They all ask the same questions and make the same stupid requests about their familes! It’s killin’ me!” He turned back to the handsome dad of four sprawled across Dean’s rack. Dean shook the bowie knife in his face. “Tsk tsk tsk.” He wagged the knife, accentuating each ‘tsk,’ “If you’re going to stay interesting to me, you’ve gotta come up with something else. It’s been two weeks and every day… It’s the same damn whines.” The man squeezed his eyes and was clearly trying to imagine himself somewhere else. “Unh-uh. None of that. I want you to see what I’m doing to you.” Dean reached up with his free hand and stretched the man’s eyes open, forcing him to peer into Dean’s soulless black wells.

                “Please. Please. I was a good man. Why am I here? Why-“ His voice broke into a sob and the whole rack shuddered with the weight of his gasps.

                “Oh, brother. That’s what they all say. You don’t get here by mistake, pal.” Dean looked back over his shoulder to Alastair, who threw an approving nod to his protégé. “Alright, well, since I’m getting so bored with you-“ The man’s eyes quickly opened, maybe with hopes that Dean would release him, or maybe in fear that something worse was to come. “I think it’s time we tried something new here.” The man winced. Something worse was coming.

                “Please…”

                “Come on now, Brady Bunch. We’re over that. You’re not getting out of Hell. We’ve been over this. “ He tapped the man’s shoulder with the knife, “I can’t get you out of Hell, but I can get you off this rack…” Dean leaned into the man’s face and flashed a toothy grin. “Whatta ya think about that?”

                The man nodded. “Please… I’m so tired. Please.”

                “Damn it! If you say ‘please’ one more time, I am going to keep you on this rack for eternity, you boring piece of shit!” Dean's black eyes were furious and he threw over the table of instruments next to him, knives and needles clattering to the ground. He really enjoyed cutting the will to live out of soul after soul, but he _hated_ it when they were so repetitious. He wanted to find new ways to break them, hear new pleas, see new versions of contorted faces. Their pain was like a drug to him and it was starting to take more and more of it for him to reach his high. Alastair interrupted his thoughts by calling him over. Dean stepped over the mess of torture devices and approached his teacher.            

                “Dean, you seem to be getting bored very easily lately.”

                “I know! I’m just so sick of the same thi-“

                “Yes, I know,” Alastair interrupted. “I want to suggest something to you in between letting this man off the rack and letting him torture a soul himself.”

                Dean’s interest was piqued. A new form of torture? Anything for that high. “I’m listening,” Dean said anxiously.

                From the rack, the family man could hear their muffled whispers and he hated the way they kept looking at him, two sets of shadeless eyes staring him down.

                When Dean returned to his side at the rack, there was a renewed fervor in his black eyes. “So, my boss over there had a great idea.” Dean raised his eyebrows at the man. “You interested?” The well-muscled man stretched out on the rack nodded reluctantly. If it got him off the rack and away from Dean’s knife, he would do anything. “Well, like I said. We can’t get you out of hell, but we _can_ get you off this rack,” Dean grabbed a beam of the rack and gave it a gentle shake for emphasis. “And as you know from your crossroads deal, demons always keep their word. You trust me so far?” A demon. A demon in Hell, who had been torturing him with a beat-up old knife for the past 14 days was asking if he _trusted_ him. The man almost wanted to roll his rich brown eyes and flash a smile, but he knew this wasn’t the time for an attitude. If they were offering a way off this rack, he was going to take it. He nodded.

                “Great!” Dean said enthusiastically. There was a dark glint in his smile that the man really didn’t like and his black eyes twinkled. He was unsure what he had just agreed to, but Dean was cutting the ropes around his hands and ankles. “Don’t think of going anywhere because all I have to do is snap my fingers and you’re back on this rack, strung up tighter than before.” Dean said in a gruff voice.  The man nodded again. He was so relieved to be free. He rubbed his arms where the rope had dug in and left bloody bracelets around his wrists. He was _not_ going back on that thing. “Alright, well let me tell you the deal.” Though Dean’s eyes were completely black, there was a hint of malice there, so foreboding that the man took a step back. “Nuh-uh, Brady Bunch. You want back on that rack?” The man gulped and stepped forward to Dean, who was a good 6 inches taller than him. The demon began to explain what waited for him and as Dean’s words sunk in, he slowly came to wish he was still roped up on that rack…

* * *

 

                “Oh, that was nice, boy.” Alastair moaned as he pulled himself out of the man’s mouth, cupping a hand under his chin. “Be sure to swallow for me.” The man closed his eyes and did as he was told. Alastair threw his head back and moaned again at the sight of the handsome man gulping down what he had spilled into his throat.

It had been a long, long time since the man had done that. Before he’d died, he had been married to a lovely woman for 9 years, but long before that he’d had a phase- A phase where he had sucked any dick he could find, a phase where he opened his legs for any man that was willing. That phase had been a hard time in his life, torn between his sexuality and the opinions of his conservative Mormon parents. That’s where the crossroads demon had come in. The smooth-talking soul salesman had promised to get rid of Matt’s gay desires and to help him get a normal life that would make his parents proud. It had been a tough decision for Matt, but his mother’s health was failing and he had wanted to make sure she died knowing her son had a family. The demon gave Matt everything he had asked for, but had never mentioned that he would be back to collect his payment in ten short years. So here he was. In a cruel ironic twist, his deal with a demon to stop sucking men off had brought him here- to sucking off two demons in hell. It was almost laughable. Almost.

“Hehmm,” Dean cleared his throat. Matt pivoted on his knees so that he was inches away from the other demon’s swollen cock. “Now, Alastair might have been gentle and let you do it your way, but I have certain expectations,” Dean sneered down at him. Without warning, Dean grabbed a fistful of the man’s tousled hair with one hand and his jaw with the other. Crouching so he could look in the man’s eyes, Dean hissed into his ear, “Make it good or I’ll chain you back to that rack over there and fuck you until you’re raw.” Matt didn’t want to be back on the rack so he slipped his tongue out and licked his lips. Maybe the demon’s deal still worked in Hell because he really wasn’t enjoying this like he used to in college. The sight of Dean’s throbbing cock and balls hanging heavy didn’t do anything for him, but he was glad he’d had practice. He was not going back on that rack so he would make it good.

He let his jaw fall slack and darted his tongue around Dean’s head, slicking around it in circles and slowly spiraling his way to the slit, where a clear bead of precome was already forming. He wasn’t sure what the demon liked so he kept trying different things until he got a reaction. He flicked his tongue violently under the edge of Dean’s head, playing with the sensitive nerves there. He licked the underside of Dean’s long shaft in one swift motion, from balls to the tip, and then moved slowly back down, spinning his tongue along the length. He pulled one of Dean’s balls into his mouth and massaged it with his tongue, first one then the other. Dean was moaning now, obviously enjoying Matt’s flat, smooth tongue. Matt continued back and forth on Dean’s balls until Dean was bucking up into him, clearly ready for a stronger sensation. Matt pulled off Dean’s balls with a filthy slurp and wet his lips again. He pressed his puckered lips to the head of Dean’s cock, slowly opening them around it as he pushed down onto Dean. The warm, wet sensation had Dean fighting to keep himself from fucking Matt’s face, but he wanted to savor this. It wasn’t everyday he got an ex-cockwhore on his rack.

Matt slowly took more and more of Dean into his mouth until Dean’s head pressed against the back of his throat and Matt’s nose was pressed firmly into Dean’s coarse hair. “Fuck……” Dean moaned, reaching a hand down into Matt’s hair. Matt started an old trick he had learned in college. With Dean’s cock still resting against the back of his throat, he began to wiggle his tongue against it, running it up and down as much as he could with his mouth so stuffed. Dean gasped and huffed out another quiet “fuck.” Matt continued this for another minute, slowly sliding his tongue across the dick in his mouth, all while Dean’s breath was becoming ragged. “Ok. You’ve had your fun. Now it’s time for mine.” Dean panted out as he took hold of hair on either side of Matt’s head. Dean pulled Matt’s hair hard, using it to pull his dick deeper and deeper into the other man’s throat. Matt blinked back tears and tried to keep his tongue swirling. He was determined to never see the rack again. “Shit…” Dean huffed as he sped up into Matt’s tight, wet throat. With a flash of his black eyes, Dean shoved Matt down to the ground and hovered over him, thrusting in and out of his mouth, fucking his face. Dean’s balls bounced against Matt’s lower lip and chin, and Dean’s dick shoved further into his throat with each thrust. Dean was on edge and Matt could sense the orgasm building up in Dean’s abdomen. Matt swirled his tongue more furiously around Dean’s shaft, creating a hot friction that zinged through Dean like an electric current. Dean was so close now. He bucked his hips faster and more erratically into Matt’s hot throat. Matt closed his lips around Dean and sucked. He brought a hand up and massaged the balls smacking against his chin. The combination of sensations- his head against the back of Matt’s throat, Matt’s tongue swirling around his shaft, Matt’s lips sucking hard around his base, and now his hands against his balls, forced Dean over the edge. “Fuck!” Dean yelled as he came. His come shot from his dick, sliding unseen down Matt’s throat.  

Dean got up and stepped over Matt, leaving him lying on the floor. “Not bad, Brady Bunch.” Dean wiped the sweat from his brow using his forearm and stared down at Matt with his deep black eyes. “But you still have the rest of our deal to come through on.”

 

 

 


	4. A New Toy

**Summary for the Chapter:**

> Cas finally finds Dean and his worst fears are confirmed. Demon Dean recalls some of the fantasies he used to have about the angel.

Castiel whisked around the corner, tattered trench coat swirling behind him. He prayed the demon hadn’t seen him. Smiting demons had become more and more difficult the closer he got to the entrance of Hell. He wasn’t sure if they placed more powerful demons near it or if he was just getting weak from killing so many, but he didn’t want to think about what either of those possibilities meant for Dean.

When he was sure the demon was not pursuing him, he continued slinking along the edge of the stone turret. Screams echoed from within the castle of Hell, calling out from racks in infinite dungeons. The air was heavy with pleas for mercy and demons’ soulless laughter. On the other side of the thick wall, Cas knew he would find hundreds of demons working over victims and he hated to think that Dean was among the torturers.

 

He no longer held out hope that Dean had resisted the powers of Hell. He had heard from far too many demons about the Master Torturer called Dean. He was almost positive that it was his Dean. He heaved with a disappointed sigh and forced the thought out of his mind. Castiel continued sneaking along the wall. With every step, the screeches and wails from within the castle got louder. The main entrance was near.

* * *

 

Dean looked back at Alastair, seeking approval from his teacher. Alastair gave Dean a knowing look.

“Feels good, doesn’t it?” Alastair pointed his chin towards the rack. “To corrupt your first soul?”

“Yeah. It really does,” Dean growled back, ink black eyes fixed on the razor blades in Matt’s hands. “Especially to corrupt it in more ways than one.”

Alastair and Dean exchanged smirks as they leaned against the dungeon wall, watching Matt and silently fantasizing about what perverse acts they’d do to him later.

 

Alastair admired what Dean had molded Matt into. He still didn’t enjoy hurting souls, but he was a great torturer because he knew what would happen if he didn’t put on a show for his overseers. Dean had made damn sure that Matt knew what was expected of him and the punishment should he fail to meet those expectations.

Matt spent most of his time running razor wire and knives and splintered shards of wood along souls on the rack. He hated it. He still winced when his victims cried out, still looked away from their contorted faces, and tried to be as gentle as Dean and Alastair would let him. But Matt knew he couldn’t disappoint his overseers or they would take it out on his ass and mouth later… So he hurt his victims as much as he could stand, praying that any pain he inflicted on them would be spared him later.

Much like Dean in the beginning, Matt favored the whip. He knew how to work it so that it didn’t inflict as much pain, but still made an intense cracking sound. Tired of the old man’s bloody yelps, he set down the razor blades and picked up the worn leather whip. He knew Dean and Alastair preferred the more hands-on torture, but he would give them a show if he had to. He was just glad he would be able to look away from the elderly man’s face as he snapped the whip back and forth across his chest.

                Cas doubled over and white flashed before his eyes as the demon crumpled to the cobblestone floor. Each demon he smited seemed to take a little more juice out of him and he was already exhausted. He had to be more careful if he was going to reach Dean.

The demons inside the castle were uncooperative and would not tell Cas where to find Alastair’s newest prodigy so he had to smite every one that he met. The red haired demon at his feet was the third demon he had killed inside and he was sure someone would discover the bodies soon. He stepped over the fire-colored hair pooled on the ground and hurried off down the hallway.

 

Dungeons were on either side and Cas could hear desperate cries and inhuman laughter in each one. He had no idea how to find Alastair and Dean in this labyrinth of torture, but he was sure they would be somewhere near the center of the castle so he hurried on.

“Matt!” Dean yelled out, a snarl on his lips. “You _know_ we don’t like the whip…”

Matt turned around, fearful. He had been caught trying to get out of torturing the old man. He rushed to set down the whip and pick up something sharper, meaner.

“Oh, I don’t think so, Matt,” Dean rasped, behind Matt now. “I know what you were up to. Hell, I used to do it myself.”

Matt flinched up at Dean, staring into the deep black eyes for some shred of humanity left.

“I’m sorry. I-“

“No, no, no. Matt. There aren’t any apologies in Hell. You were trying to trick me and now you’re going to be punished.”

Matt dropped the shards of glass that he had been fumbling with and his eyes fell to the ground. With a snap of Dean’s fingers, the elderly man on the rack had disappeared, zapped back to some dungeon to await the next session.

“Kneel down,” Dean ordered. “Since you don’t know how to make someone hurt, we’re going to teach you.” Alastair stepped up alongside Dean and flashed a sick smile at Matt.

 

Matt gritted his teeth and slowly fell to his knees. This was going to be a rough night.

Cas stopped. Was that? No. He wasn’t anywhere near the center of the castle yet. Or at least he didn’t think so. He tried to mentally map where he was and determined he still had a long way before he reached the middle of the vast fortress. But that sounded so much like Dean’s voice…

Cas looked both ways, scanning the long dark hallway for any figures. When he saw none, he backed up a few steps to a large wooden door. He peered through the metal bars across the top of the door and fought to make out shapes in the dark room. He thought he could make out two figures, both with their backs to him.

As his eyes adjusted to the dim torchlight in the room, he determined there were actually three figures in the room. One was kneeling before two tall male forms. Cas didn’t recognize the taller one, but the slightly shorter one had a familiar build. Slightly bowed legs, a narrow waist, and square shoulders… Cas’s heart sped up in his chest, but he wasn’t sure yet.

Cas jumped when a cry rang out from the taller figure. Cas hurriedly slouched down, worried he had been spotted between the iron bars. He didn’t hear any footsteps nearing the door so he slowly rose back up. The tall figure’s head was thrown back and Cas’s eyes fell to the figure kneeling before it. He realized what was happening in this dungeon and grimaced. This was a new low, even for demons.

Disgusted, he fought the dark desperately, trying to convince himself the other figure wasn’t Dean. Even as a demon, surely Dean wouldn’t do _this._ Cas’s hopes were shattered when the other figure turned to the side. Cas recognized the profile, silhouetted against the torchlight. The defined jaw line and straight nose could only belong to one person. They were distinctly Dean Winchester’s.

 

A long breath escaped from Cas, almost a sigh, almost a whimper, because even in the low light, Cas realized something was wrong with Dean’s eyes. The bright eyes that normally sparkled green instead absorbed all the light around them. They were a deep inky black, devoid of emotion or empathy, and they made Castiel sick.

On the other side of the door, Matt swallowed reluctantly. His throat was raw and his lips had been painfully stretched, leaving him cracked and bleeding, but it wasn’t over yet. He shuffled nearer to Dean and prepared to satisfy the second demon. He was interrupted.

“Dean,” Alastair said lazily, “I think you’ve got it under control here, right?” Alastair’s eyes flashed something that Matt couldn’t read.

“Oh, yeah. Everything’s under control,” Dean replied, smiling at Matt, emphasis on the word ‘control.’

Matt’s heart beat faster, terrified for what new torture Dean had come up with.

“I’m gonna head out, but I’ll see both of you tomorrow for another exciting day.” Alastair winked coldly at Matt and slapped Dean on the shoulder as he made his way for the door.

Cas tensed when he realized the tall demon was Alastair and he was coming for the door. Cas hurried out of the door’s alcove and hid in one down the hall, praying the demon was going the other direction. He crouched in the corner and made himself as small as possible.

The demon passed by him without noticing and Cas let out a breath of relief. This situation was very, very bad, but at least it hadn’t gotten worse. He straightened himself and checked down the hallway for any signs of movement. Alastair had disappeared down another corridor somewhere and Cas returned to the door hiding Dean.

Cas was unsure what his next move should be. He peeked through the iron bars again, watching Dean and the other figure intently. Dean had pulled the kneeling figure up and Cas now recognized it as a male, but it wasn’t anyone he knew. Cas looked on anxiously as Dean fumbled with the buckle on his belt. Cas lurched for the door handle before he knew what he was doing. He grabbed the iron handle of the rough wooden door and slammed it open.

The unknown male saw Castiel first and jumped back, away from Dean and away from the door. Dean swiveled around angrily, teeth bared and dark eyes flashing. He took a step toward the intruder, but stopped midstride when he recognized the angel scanning the room wildly.

“You,” he growled out, lips curling and nostrils flaring.

“Yes, Dean,” Cas said evenly, trying to stay calm. He had no idea what to do now that he had burst into the room.

Dean walked closer to Cas, eyeing him up and down, moving in wide circles around the angel. “Why are you here?” he asked in a mean, gravelly voice.

Cas, normally cool and confident, wriggled his hands nervously in the pocket of the trench coat. He felt the cool metal of the angel blade against his wrist. It was reassuring, but he knew he would not use the blade on Dean, no matter what happened down here.

“Answer me!” Dean shouted, nearing Castiel’s face.

Cas stared into the black pits, searching desperately for some fragment of the Dean he knew. “I came to rescue you. Again.” Cas swallowed and steeled his jaw. “I see I was too late this time.”

Dean threw his head back in laughter. “And what makes you think I want that, Angel of the Lord?” Dean’s tone was icy and cruel. “I’ve finally let go of everything.” He stepped even closer to the angel, now just inches from Cas’s face. “I quit caring.” Dean spun on his heels and looked back over his shoulder to Castiel, black eyes glinting. “So should you.”

“Dean…” Cas swallowed. The guilt he felt was crushing him, but he fought it. “Dean, I am going to fix this.”

“Oh-ho, Angel!” Dean was heading for Matt, fumbling with his belt buckle again. “There’s nothing to fix. This is the best I’ve felt in years.” Matt cowered away from Dean. He was distracted by this new being in the room and thought it might be a good opportunity to get away.

Cas remained in the middle of the room, plans racing through his mind. How could he rescue Dean when his angel powers were so weak?

“Be still!” Dean grunted at Matt. Dean had picked Matt up and bent him over the table that held all of the torture instruments. Fractures of glass and shrapnel threatened to cut into Matt’s face as Dean pressed him down.

“Dean! This is not you!” Cas shouted, taking strides toward the demon. “Stop!”

Dean swiveled on his heels again, visibly irritated that the angel was still there. He stared Castiel down for a minute before a flash of something leapt across his face. He paced towards the angel, bringing them only a foot apart. Cas didn’t like the look in Dean’s raven eyes and took a step back. Dean matched his step and closed the gap between them. Dean’s lips stretched into a crooked smile and his tongue darted out to wet them.

“You’re right, Castiel.” His voice slid out of his lips, smooth and inky, and somehow unsettlingly calm. “This isn’t me.” Castiel raised his hand and tried to take another step back, but Dean grabbed his wrist firmly. Cas’s face was washed with surprise and fear.

“It isn’t me, Cas.” Dean said the angel’s nickname with animosity. “And that’s a good thing.” His eyes were gleaming with something new now and Cas’s stomach turned. This was bad. Very bad.

“ See, the old me had some strong feelings for you, Cassy.” Dean’s voice was cold and littered with condescension. “And not just the ‘this is my angel knight in shining armor turned best friend’ kind of feelings…” Cas looked into Dean’s black eyes, confused, and tried to rip his wrist out of the demon’s strong grip. Dean squeezed tighter and pulled Cas so that their faces were inches apart. “No, sir. Our boy has been denying some **pretty** dirty thoughts about you and that angel mojo. They’re downright raunchy.”

Cas squirmed under Dean’s hold. What was the demon saying? Surely some of Dean’s consciousness was in there somewhere.  “Dean, you can’t-“

“Filthy, even. Oh, some of those dreams we had about you and what you might be capable of with those powers- almost enough to make a demon blush. Oh, we wanted to fuck you so bad. Just rip up that angel innocence like it was nothing...” Dean continued, ignoring Castiel. The demon was much stronger than Cas, especially with his weakened powers. “But we always had to fight those feelings up there. Down here, there’s no such thing as wrong… “

Dean was dragging Castiel towards the rack and table, where Matt sat on the floor wide-eyed. Castiel fought against the demon, digging his heels into the ground, throwing his weight against Dean, but it had no effect. “Dean, listen! I know you’re in there somewhere. You don’t want to be like this. You don’t have to do this. Let me help you.” Cas’s voice sounded muffled in the stone dungeon and Dean easily ignored it.

“Matt, get up.” Dean said coolly. Matt did as he was asked, staring at the ground, afraid of what was to come. “You’re done for tonight.” Dean snapped his fingers and Matt disappeared to his holding cell.

Dean wrenched Cas around in his grip, so that the two were facing each other. Dean’s solid black eyes burned with malice as they took in Cas. There was something smoldering under the surface too, something Cas might have recognized as lust if he had been able to focus on anything other than his own fear.

Dean licked his lips again and whispered to an unseen audience, “I’ve found a new toy.”


	5. Digging In

**Summary for the Chapter:**

> Cas’s thoughts were interrupted when he heard a clatter. He looked up to see Dean had dropped the knife back on the table and was peering at him with onyx eyes. “I’m all for a little torture. Like I said, I’ve never tortured an angel before.” Oh, God. Cas squinted his eyes, bracing himself for whatever came next. “But I want to play fair since we go way back, buddy.” Cas opened one eye. Why the fuck is Dean messing with me like this?  
> “So here’s how it’s gonna go. You’re going to do whatever I ask and answer all my questions.” Dean turned his back to the angel, fiddling with something on the table. He turned back around, hiding something in his big hands. “And if you don’t play along…” Dean held up his hand, revealing the pair of scissors again, opening and closing them, “I’m gonna make you hurt.”

**Notes for the Chapter:**

> Sorry this is a few days late, but I went the extra mile to make up for it! This chapter is LONG, has HINTS of emotional stuff to it (okay as much fluff as you can get with a demon in Hell, okay...), AND FINALLY some Dean-on-Cas smut.  
> Thanks again for all of your kudos and bookmarks and comments! This is my primary fic right now and your encouragement helps me stay inspired! :)
> 
> Warning! There is knife play, torture-y stuff in this chapter. It's mild and there isn't any blood or gore, but I'd rather warn you excessively than trigger or offend someone!

                Cas’s eyes widened and his jaw fell slack. His eyes darted back and forth between Dean’s, but there was nothing but black lust there. “Dean, let go of me. I don’t want to hurt you,” Cas said sternly.  He thought about what little he could do. His weakened powers felt useless here, but maybe Dean didn’t know that.

                The lascivious look on Dean’s face melted away into a mocking smile. “Oh, okay. I’ll just let you go, here and now. Off on your way then!” Dean shrugged, released Castiel from his grip, and gave him a shove toward the door. Cas stumbled and turned back around, brows dropped in confusion.

                “Dean. I am not leaving Hell without you. I am going to-“

                “Oh, that’s right! You're gonna grip me tight and raise me from perdition again. Let me just pack up my things and I’ll be glad to go with ya, bud,” Dean said in a mocking and sardonic tone. He turned to the table and grabbed his favorite rusted and chipped knife. “Okay! All set!” Dean’s sarcastic enthusiasm hurt Cas. It almost sounded like something his Dean would say, but it was laced with dark intentions, a cruel reminder that this was a twisted version of the Dean Winchester he knew.

                As if he could read Cas’s mind, Dean called out gruffly from the table, “Something wrong, angel boy?”  Cas remained in the middle of the room, a wild mix of confusion, concern, and fear over his face.

He didn’t know how to react to this Dean. When he had first arrived in Hell, he still held out hope that he would find Dean on a rack somewhere. He would smite the torturer, and carry the righteous man out once more. After he was repeatedly assured Dean was in fact a torturer himself, he formed a new plan. He was prepared to fight Dean and somehow use his grace to revert Dean to his old self. He had been ready for a challenge to get his friend back, but he had no idea how to interpret Dean’s seemingly willing attitude.

                _He is up to something, but what? What is he toying at?_ No way would a demon choose to leave Hell with an angel, even if it was Dean and Cas. “Dean, I do not understand,” Castiel started.

                “I just… have missed you so much, Cassy,” Dean said with a fake sincerity and a little pout. “I haven’t been able to stop thinking about you and all the fun adventures we had up there, Dean fluttered his eyelashes at Cas, "and the looks you used to give me with those blue eyes,” Dean sighed. “No one looks at me like that down here. No one _loves_ me here.” Dean paused and looked at Cas with pleading black eyes. “ Isn’t that right, Cas? You love me, don’t you?”

                Cas felt his gut hitch and the color pooled out of his face. _How do demons know everything?_ “Dean, you are my friend and it is no secret that I care too much, but-“

                “Oh, but Cas… That’s not what I asked, now is it?” a tinge of gravelly animosity coming through again. Dean took strides toward the angel, wagging the Bowie knife as he did so. “No. I know. Actually, I think I always had some kind of inkling up there,” Dean pointed his eyes to the ceiling, “but down here… “Dean’s eyes locked on to Cas’s and his voice became deeper, taunting, “Down here, everything is so much clearer. I _know._ ”

                _So that’s what Dean is doing. He is going to mess with me like **that.**_ Cas swallowed and took a step back, afraid of what physical torture might come with this emotional abuse. Dean stepped closer and Cas's eyes flickered to the knife still in Dean’s hand. Dean noticed and shifted his own eyes to the knife.

 

                “Are you scared of the knife, Cas? Don’t worry. It can’t hurt you.” Dean’s black eyes flickered, rich with malice, back to the angel’s deep blue ones. He opened his fingers around the knife and let it clatter to the stone floor, the noise echoing off the walls. His eyes narrowed on Cas and a low voice slithered out of him, dark and cold, “But I can.”

* * *

 

                Cas woke up coughing and sputtering. His eyes darted around the room, making out his trench coat crumpled on the floor. Besides the khaki coat, the dark dungeon appeared empty. He was choking around what tasted like a piece of leather and he reached to pull it from his face. His wrists stopped abruptly, restrained by thick straps. He groaned around the leather and tried to call on his angelic strength to break the bonds, but his powers faltered. He was just too weak. He breathed heavily around the leather and strained to move his ankles and wrists. “Dean!” he cried out, muffled by the wad of leather in his throat.

                “Good morning, sunshine,” Dean sneered from behind him.  Cas tried to wretch his head to peer back at the demon, but stopped short, cringing at a pulsing pain in his temple. He remembered Dean striking him to the floor easily earlier. It must have knocked him out. Cas cursed in his thoughts.  _What the hell is Dean doing?_

                “Glad you’re up. Sure have missed your company!” Dean said in that same cold and sarcastic tone Cas had heard him use with demons and vampires and asshole angels many times before. Cas wondered what Dean was doing back there. He fought the straps at his wrists again and said something curt to Dean, muffled by the gag.

                “What’s that? Did you sleep okay? You must have since I was able to tie you up like this and you didn’t seem to mind a bit.”Dean peeked his head around the edge of the rack, staring at Cas with black soulless eyes. “But now that you’re up,” Dean raised his shoulders and smirked at Cas, “let’s have a chat.” He clapped Cas on the shoulder and moved to pull up the table.

                Cas stared with wide eyes as Dean pulled the table full of tools aside the rack. Dean picked up a rusted pair of scissors and quickly opened and closed them. Glancing at Cas, he whispered, “Ya know, I’ve never tortured an angel.” Cas’s protests were muffled by the skin in his mouth as Dean stepped up to the sprawled angel.

                Dean dragged the scissors down Castiel’s chest, the sharp tip catching on the rumpled fabric of his shirt and tie. Black eyes flashed to Cas’s, taking in the fear there like some kind of intoxicating fuel. Cas’s chest was falling fast with his breaths and his eyes darted quickly between Dean’s, seeking some of Dean’s former mercy.

                Dean grabbed Cas’s tie abruptly. “I’m just fuckin’ with ya, Cas.” Dean’s black eyes stared Cas down and Dean wet his lips, tie still in hand. Without taking his eyes from Cas’s, Dean snipped the tie off right below the knot and worked the strip of cheap silk loose from the angel’s neck. Cas was breathing heavily and did not feel as relieved as he should at the demon’s words.  Cas couldn’t voice his questions, so instead he lowered his brows and narrowed his eyes.

                “I just think this conversation would be easier if you were more comfortable, that’s all,” Dean said through a sideways smirk. Dean turned his black eyes to the wrinkled white shirt clinging to Cas. He put the scissors in his mouth to free both hands. With a quick glance at Cas’s panicked eyes, Dean worked at the dress shirt, pulling it from Cas’s slacks roughly. He reached around to the small of Cas’s back to pull the tail of the shirt out, leaning nearer to Cas’s ear as he did so. “I thought about this a lot up top,” he gruffly whispered in Cas’s ear.   

                A shudder moved up and down Cas’s spine. _What is Dean saying? What?_ His thoughts raced. He was confused and scared by the demon’s words, and, he shamefully admitted to himself, a little intrigued. _Dean used to think about me? Like this?_

Before Castiel had enough time to process what he had just thought, Dean was working the scissors up the front of the shirt, ignoring the buttons, and ripping the fabric off the angel with ease. Cas was left with two ragged sleeves and a bare torso, heaving deeply.

Dean ran the back of his fingers up the angel’s chest, lips curling at the edges. Cas shut his eyes tight and bit down on the ball of leather, just waiting for the dig of sharp metal into his skin, but it never came. Instead he heard the scissors cutting through the fabric around his arms, freeing him completely from the remnants of his shirt.

                “Much better,” Dean purred quietly, stepping back to admire the angel stretched out before him. As a human, Dean had never had much occasion to fully check out Cas. Sure, he had taken sideways glances here and there, but never like this. There were no clothes in the way. There was no voice in his head yelling at him to knock it off and man up. There was no guilt that this was an angel of the Lord. There was no shame that they were both men. Dean could just admire the body before him like he’d always wanted to.

                Cas heard Dean step back and he opened his eyes hesitantly. Dean’s inky eyes were crawling over him hungrily. They trailed along his lean, but well-muscled biceps and chest, down his abdomen and lingered on the sharp V of his hipbones disappearing inside the low-slung pants.  Cas didn’t know how he felt about this. Part of him felt ashamed that his friend was looking at him like this, but deep below that he felt a tinge of excitement. It prickled the hairs at the back of his neck and made his ears blush red and he didn’t know why. He felt scared, but at the same time he was fascinated by the sensation starting in his stomach.

                “So about that chat, Cas,” Dean uttered with a wink and smirk. His dark eyes were still glinting at Cas sadistically, but right under the surface there was something else. Despite black soulless eyes without emotion, Cas could recognize it. It was the way he had looked at Dean many times before, even if it was tainted with malice and hurtful intent. It was longing.

                Dean pulled up the table closer so he was within arm’s reach of the angel. He sat perched on the edge, facing Cas and his eyes still trailed over Cas’s pale abs. Cas felt himself blush, but he didn’t know if it was fear or something else. He forced himself to ignore the sensation and tried to ask Dean what he was doing but all that came out was a stifled syllable or two.

 “If you promise to behave, I’ll get rid of that gag, buddy.” Cas nodded and Dean stood to cut the leather strip away using his broken knife. Cas spit and coughed, licking the taste of leather from his teeth. “Dean, what the hell is going on?” he yelled angrily. “Untie me!”  

                “Hey! I said if you _behaved._ Shut the fuck up!” Any semblance of friendliness Dean had shown before was gone. Cas had trouble remembering that this was absolutely not his Dean. The mannerisms were the same and his memories were there, but this was a mean, heartless, and perverted version of the hunter. Anything could set him off and bring out the side that wanted to hurt and use him.

                “Are you gonna behave?” Dean asked with a rude nod of his head.

                “Yes,” Cas said in a deep voice. He shifted his eyes down in resentful defeat. He was scared of Dean’s idea of good behavior.

                “Alright then.” Dean sat back on the edge of the table and absentmindedly fingered the knife in his hands. He flashed Cas a devilish grin and Cas was surprised at how quickly this demon Dean could go from fits of anger to this mocking kindness. “About that chat…” Dean trailed off and looked down at the knife in his hands, lips pursed. _This is it. He is going to torture me. Dean is completely gone._

                Cas’s thoughts were interrupted when he heard a clatter. He looked up to see Dean had dropped the knife back on the table and was peering at him with onyx eyes. “I’m all for a little torture. Like I said, I’ve never tortured an angel before.” _Oh, God._ Cas squinted his eyes, bracing himself for whatever came next. “But I want to play fair since we go way back, buddy.” Cas opened one eye. _Why the fuck is Dean messing with me like this?_

                “So here’s how it’s gonna go. You’re going to do whatever I ask and answer all my questions.” Dean turned his back to the angel, fiddling with something on the table. He turned back around, hiding something in his big hands. “And if you don’t play along…” Dean held up his hands, revealing the pair of scissors again, opening and closing them, “I’m gonna make you hurt.”

                Cas swallowed. He couldn’t take his eyes off the pair of shiny scissors in Dean’s hands just inches from his face. “Got that, wings?” Cas nodded slowly. He wasn’t happy about it, but he figured playing along was his best shot. Maybe this would give him time to get his strength back and if he could do that he still had a chance to get Dean out of here.

                “Great!” Dean barked. He pulled the table so it was no longer at the side of the rack, but squarely in front of Cas. With a sweep of his arm, he cleared the table of most of the tools and they fell to the ground noisily. He hopped back on the edge of the table, a knee on either side of Cas, pressing into his hipbones. Cas felt his breathing pick up again, a weird mix of fear and adrenaline running through his veins. _This isn’t your Dean, Cas. This isn’t how it’s supposed to be._

Cas had often thought of Dean touching him like this. Simple touches, small fleeting ones, happened sometimes. Quick embraces, a pat on the back, a hand clapped to his shoulder. Cas knew they were gestures of friendship and probably meant nothing special to the hunter, but they were important to Castiel. They were signs that Dean cared about him.

He had been deprived of touch most of his angel life and these little moments of contact always left him wanting more.  Many times he had found his thoughts wandering back to images of Dean’s hands on his shoulders or the hunter’s strong arms around him. They made a warmth bloom in his chest, a  warmth he wanted more of. Alone in his thoughts, he had chased that high several times, picturing Dean’s hands clasped on him, touching him, skin against skin. These thoughts stirred something else in Cas, something he never allowed himself to give in to. He always drew himself back before he went there.

“Ya still with me, Cas?” Dean asked sarcastically, tipping the angel’s head up with the blunt outside edge of the scissors. Cas snapped out of it and looked up into Dean’s eyes. He nodded, fearing what would happen if he let himself drift again. _Just go along with Dean’s game for now and get your strength back._

“Okay then. You know the deal. I ask, you answer, and these scissors don’t have to hurt this pretty vessel of yours.” Dean drew the scissors lightly all the way down Cas’s bare chest for emphasis. He started at his collar bone and stopped right above the hem of Cas’s pants, leaving a faint red scratch the length of Cas’s body. It wasn’t enough to hurt, but the sensation quickened the angel’s breath.

Dean licked his lips and ran the edge of the scissors along the edge of his victim’s trousers. Cas’s abdomen twitched under the light touch, unsure of what Dean was doing. He was scared, but deep down he was pretty sure Dean would not hurt him, demon or not. He felt a hint of a thrill under his fear. Having his friend’s eyes on him like this excited him, even if it wasn’t the Dean he knew.

“First question,” Dean said evenly. His eyes were full of malicious mischief and a small spiteful smile sat on his lips. Cas gulped, unready for what came next. “Tell me, angel, how do you really feel about the hunter Dean Winchester?”

Cas blinked. _That was it? That was all Dean was going to do? Ask him questions?_ His thoughts were cut short when he felt a gentle stab below his navel. _Fuck!_

“Come on, angel! Answer the question or I’m diggin’ in!”

 _Shit. Shit._ Cas’s mind raced, trying to think of a satisfactory answer to the demon’s question. He didn’t want to say the wrong thing and feel the scissors push through his flesh. “What do you mean?”

“Nope! I’m askin’ the questions here, pal. Try again!” Dean pressed the scissors deeper, not far enough to break the skin, but enough to hurt. Cas winced.

“Dean! I don’t understand! Don’t you know?!” Cas blurted. His chest heaved. He was full of fear, anticipating the sharp bite of metal any second now.

“Sure!” Dean moved his face closer to the angel’s. “But I want to hear you _say it,”_ he snarled.

For the first time in his entire existence, Cas felt a reluctance to say what was on his mind. Normally he said things without a second thought, but he felt a hesitation in his voice, embarrassment. “Dean… You are my closest friend, my only friend.” Cas looked up into Dean’s ebony eyes, seeking approval at his answer.

“Nice try, but it’s not just friendship, is it?” Dean pressed the tip of the scissors deeper, breaking the soft white skin on Cas’s stomach. Cas squeezed his eyes shut and gritted his teeth.

“No! No, I don’t know. I don’t know what it is, Dean! Please!” Cas said quickly. The demon pulled back the scissors, admiring the red mark he’d left on the angel.

Dean’s eyes stared into Cas’s blue ones. “All right. All right!” Dean said, pulling back and raising his hands animatedly. “So you don’t have a word for it.” Dean stood, filling the small space between Castiel and the table. He pressed his body against Cas. He was inches from Cas’s face, eye to eye, and the demon’s lip twitched. “How about you tell me how I make you _feel?”_ With the last word, Dean pressed a palm against Castiel’s crotch, squeezing a handful of the angel.

Cas’s eyes flew wide open and darted between Dean’s black ones. His breath escaped him and his nostrils flared in panic. He was always hungry for Dean’s touch, a hug or a friendly slap, but he never let himself go this far in his mind. Sure, in some dark corners, he had wondered about it- his hunter’s hands on his most sensitive skin, but he always forced the thoughts from his mind. Dean was his friend and he shouldn’t think about him that way, especially now.

“Huh?” Dean prodded, squeezing harder. Cas drew a sharp breath, eyelids briefly fluttering.

“I-I don’t- know,” Cas huffed, trying to ignore the ripple of excitement he felt under his skin. He felt blood rushing to his dick and tried to ignore the fingers kneading it slowly. “Dean…” he panted.

“You like this, Cas?” Dean’s tongue ran over his lips, watching Cas’s strained face. “I can tell you do.” Cas’s eyes were squeezed shut in reluctant enjoyment. He shouldn’t be enjoying this. This was so wrong. “Come on, Cas. Tell me how it feels.” Dean moved his hand a little faster, rubbing Cas through the smooth fabric of his slacks. “I know you’ve thought about it before.” Dean’s voice was taunting as he whispered in Cas’s ear, hand rubbing back and forth on the angel’s hardening dick.

“I- have.” Cas managed between quick breaths. He had never been touched like this before and it was flooding him with new sensations, sensations that were threatening to overtake his rational mind. He started to let the feeling take over, but was interrupted when he felt Dean’s hand leave him. His dick was hard now, beginning to throb, and Cas strained for more feeling. He opened his eyes to Dean’s raven eyes.

“Tell me about them, Cas,” Dean urged, biting his lip and glaring at Cas with narrow eyes.

Cas’s chest was heaving, short breaths rushing through his parted lips. _What is this? What is Dean doing? This feels… But it’s wrong. I shouldn’t let Dean do this._ “Dean… What?” Cas’s mind raced. He wanted to tell Dean to stop, to make him quit, but he couldn’t ignore his throbbing dick. It strained against his baggy pants, pulling the fabric, and distracting Cas from rational thought.

Dean leaned in to Cas’s ear, lips brushing the skin right before it. “Tell me…” He pressed his mouth closer to Cas’s ear. “About the times you’ve thought about this,” Dean growled. Cas’s stomach hitched. He felt the sharp tip of the scissors against his abs again.

“I- I like when you touch me, Dean,” Cas said, eyes shifting to the floor. He still felt wrong, but he felt his face flush with excitement as he said the words. He tried to convince himself he was only doing this so Dean wouldn’t stab him. _This is all part of Dean’s game. Just go along with it._

“And…?” Dean said with a nod to the bulge between Cas’s legs.

Cas took a shuddering breath and swallowed hard, exhaling as he did. “I want you…,” he looked up at his perverted torturer, “to keep touching me.”

A sick smile crawled across Dean’s lips. “That’s what I thought, Cas.” Dean took a step back and set the scissors on the table. He kicked his shoes and socks off and turned back to Cas, onyx eyes flashing. His hands dropped to the buttons on his jeans. “Wanna see?” He raised his eyebrows to the angel.

Cas’s eyes scanned the demon quickly. _What did Dean just say?_ “Dean…?” Cas licked his lips worriedly. He really wasn’t sure about this. He had wondered about it, but he had never let his thoughts reach this far. His eyes followed the hunter’s hands as they popped the button through the hole and moved on to the zipper. Cas’s breathing sped up and his mouth felt dry. He had never thought about Dean’s dick, but now he couldn’t ignore the way those thoughts made his own dick twitch. “Please…” he huffed quietly.

 Dean had his pants unzipped entirely and slid them over his hips as the angel watched intently. Cas’s eyes were fixed on the thin fabric of Dean’s boxers and the bulge fighting against it. Blood rushed to his dick, making his head swim. He licked his lips again, but his mouth was dry and it didn’t help.

Dean stepped out of his jeans and moved closer to Cas. As he did so, he grabbed the hem of his shirt and pulled it up over his head, leaving the demon bare except for the deep red boxers hugging his hips. Dark eyes stared at Cas as he surveyed the demon’s body. He wanted to touch all that skin. The taut skin over Dean’s strong arms, his rippling abs, the jut of his hip bones. Cas swallowed hard as he took it in with hungry eyes.

“Now, Cas….” Dean said in a soft, low voice. He raised a hand to hover over Cas’s throbbing dick. Cas squirmed, sharp breaths leaving his nostrils. “If I cut you down, you’re not going to run away, are you?” Cas’s eyes met the black pits glaring tauntingly at him and shook his head. Cas had entirely forgotten trying to escape. He was too enthralled by what was happening between him and the hunter.

“Good. Good,” Dean purred, brushing his hand over Castiel’s dick. He reached behind him and grabbed the knife. He drew it lightly across Cas’s collar bone and up his neck, letting it rest under Cas’s jaw. He leaned in to Cas’s face. “Do not try anything or I will make you regret it,” Dean growled. Cas nodded gently, wary of the blade pressed to his skin. Dean, seemingly satisfied that Cas wouldn’t try anything, bent to cut the straps holding Cas’s ankles in place.

As Dean straightened, he lingered near Cas’s groin, briefly running his mouth over the fabric pressed against Cas’s dick. Cas squirmed, anxious for any kind of sensation to relieve the pressure building deep in his torso. Dean stood with a smirk and worked the knife over the ends of the straps attached to the rack. He left them tied around Cas’s wrists, lengths of leather hanging off the angel. “These might come in handy.” He winked at Cas as the angel rolled his sore shoulders.

Cas stood there breathing heavily, anxiously waiting on Dean’s next move. Dean’s back was to him and Cas could make out the demon fumbling with something on the table. He wrung his hands nervously. _What am I doing?_ He knew he should be trying to capture Dean or testing the strength of his angel powers or even running away, but he felt locked in place. He wouldn’t confess it to himself, but his pulse was still beating rapidly between his legs and he wanted to see where this was going.

Dean turned back to Castiel, the dim dungeon lighting capturing his abs and pecs. Cas wanted to touch it so badly, but he was afraid to do anything without Dean’s permission. Instead he waited for Dean to reach him. Dean stood before the shirtless angel, a sideways grin etched over his features. “Still want me to touch you?” Dean whispered in a gravelly voice.

Cas blurted out a “Yes” before he even had time to think about it. “Please, Dean.”

Dean smirked, pleased with the angel’s response. “I will, but first…,” Dean’s black eyes flashed wildly over Cas and he stepped behind the angel. Cas turned to follow Dean, but the hunter put an arm on his shoulder holding him in place. Cas turned back nervously. He jumped when he felt his arms wrenched roughly behind him. Dean had grabbed the strips of leather dangling from his wrists and was tying them tightly around both of Castiel’s arms. When he realized what was happening he took a step forward. “Unh uh!” Dean grunted and jerked him back, pulling the bonds tighter.

When Dean was satisfied the knots were secured he stood back to admire his work. He reached forward and grabbed the angel’s ass, eliciting a yelp and a jump from him. The demon chuckled cruelly and reached a hand around to Cas’s belt. Dean was still behind Cas and pressed against him while he fumbled with the belt.  Cas looked down quickly, chest rising and falling rapidly as he watched Dean’s hands loosen his belt buckle. He wriggled his hands, irritated that he couldn’t help the demon.

“Calm down!” Dean barked roughly. Cas was reminded by his tone that this wasn’t Dean. This was a demonic version of him and he needed to be careful. Cas straightened his posture and stood perfectly still as the demon pulled the belt from its loops. Cas’s cock jumped in anticipation. Even if this was a warped Dean, he was still going to touch Cas and Cas couldn’t wait.

Dean circled around until he was facing the angel. Cas opened his mouth to say something but the demon snarled at him and Cas fell silent. Cas strained against his bindings as Dean undid the slacks hanging loosely off Castiel. _You’re so slow. Get me out of these damned straps!_ Dean gave Cas a warning scowl and shoved the pants to the floor. He grabbed Cas’s hips and directed the angel to step forward out of them.

Cas felt exposed. There was so much skin in the room now. Both of them stood in boxers and all Cas wanted to do was press all of their bare flesh together. He felt restricted, by both the leather around his wrists and the thin cotton around his hips. He looked at Dean, searching for some kind of hint. _What do I do now?_ Dean flashed a wicked smile at the angel and fell to his knees before him. Cas’s  breath caught in his throat. “Dean?”

“Have you ever thought about _this_ , Castiel?” Dean placed a hand on each of the angel’s hips and dug his fingers into the elastic waistband of his boxers, tugging them down. Cas gasped at what his friend had just done. He felt a sharp pain on his thigh and realized Dean had pinched him.

“Answer me!” Dean grunted from the floor.

Between ragged breaths, Cas muttered, “I do not think so.” The angel shrugged slightly, afraid his answer would upset Dean.

Dean glanced up at him, solid eyes alight with some kind of evil playfulness. “All that time up top and you still never got your dick wet, huh?” Dean raised an eyebrow, obviously soliciting an answer.

“No, Dean.” Cas answered calmly despite his racing heart. _What is he about to do?_ Cas’s mind was ablaze with thoughts dictated by his erect cock. He chewed his lip. _Should I?_ Cas decided against his rational mind and let his dick lead him. “Dean...” He swallowed. “Please.” Cas squeezed his eyes shut, anticipating a slap or curse from Dean.

But it never came. Instead, Cas was rewarded with a firm hand around his dick. Cas gasped. No one had ever touched him like that before and it sucked all the breath from his lungs. His eyes flashed open and darted down to see Dean’s strong hands pumping him slowly, toying with a lazy semblance of  rhythm. A bead of clear precome formed on the tip. Cas’s jaw fell open and his breaths became quick and uneven. “Dean…”

Dean’s black eyes flickered up to meet his, a depraved smile curling his lips. Dean tightened his grip around Cas’s shaft, moving his hand all the way from the base to the tip with each tug of his wrist. Cas’s abdomen tightened and he felt his knees go weak under him. Dean’s pace increased and Cas threw his head back, letting the feeling wash over him. This was unlike anything he had imagined.

Cas cried out when he felt Dean’s lips brush against his swollen head. “Dean!” He tugged against his bonds, anxious for release.

“Not yet,” came Dean’s low voice, raspy with lust. “Not yet.” Dean continued his quickened pace, running a finger over Castiel’s head each time he reached the top of his stroke. Cas whimpered when he felt Dean’s other hand rise up to his balls. The demon squeezed gently and tugged them complementary to his other twisting hand. Cas felt a wave of heat building in his stomach and he panted in time with Dean’s hands.

Dean looked up, grinning wildly that he was corrupting an angel of the Lord like this. The angel’s head was thrown back, eyes shut and mouth open, gasping for breath. Dean recalled all the times he had pictured Castiel like that, images he had formed long before he had become a demon. The mental images had been pretty good, but they hadn’t come close to what he was seeing before him right now. Dean felt his cock jump at the thoughts of what he was going to do to the angel later.

For now though, he had other plans. He licked his lips and pressed them to the tip of Castiel’s dick. The angel’s head snapped down, eyes wide, staring at what the hunter-turned-demon was doing now.  “Fuck!” slipped out of Cas as Dean parted his lips and took him slowly in to his mouth. Dean didn’t waste any time because he was ready for it to be his turn. With one hand still working Cas’s balls and the other bracing himself, Dean slid his lips all the way to the base and held there, running his tongue up and down the length of Cas’s shaft. Cas moaned and panted, fighting his restraints, desperate to hold Dean’s mouth in place.

Dean tugged on Cas’s balls harder and bobbed his head up and down on Cas to match that pace. Cas felt unsteady and wished he could brace himself. He was merciless at Dean’s lips and any thoughts he’d had about this being wrong were dissolved by Dean’s smooth tongue licking the length of his dick. The wave of heat in Cas’s torso picked up speed and Cas rocked with it, pressing himself further into Dean’s mouth. The demon moaned around Cas’s cock and swirled his tongue viciously around the head.

Cas’s breaths were shallow and uneven and he longed to dig a hand into Dean’s hair and pull himself deeper. Cas wasn’t thinking about Dean being a demon or how he was eventually going to rescue the hunter. He wasn’t thinking about how wrong this should feel or the fact that he was an angel getting sucked off with a demon. All of Cas’s thoughts were replaced with the lewd slurping of Dean’s lips around him. It was all Cas could think about and it made his head swim and his heart pound.

Dean sucked a little harder and maintained his steady rhythm, subtly slipping his hand from Cas’s balls and pressing further back. Cas gasped, but made no effort to resist Dean’s insisting hand. Dean quickly brought his finger to his mouth, gathering wetness from it, and returned to Cas’s hole. He circled the tight circle, pressing against it in time with his still-bobbing lips. Cas moaned and thrusted gently into Dean, angry that his hands were not free to touch the demon.

Dean looked up at Cas, onyx eyes ablaze with lust, smiling wickedly around the angel’s dick. The servant of Heaven was completely at his mercy right now and that was exactly where Dean wanted him. Without warning, Dean crooked his finger into Cas, pressing deep and fighting the resistance he found there. Cas’s eyes flew open and he sucked in a deep breath as he snapped his neck to look at Dean. Cas was met with an unforgiving stare from those solid eyes.  The pressure building in his groin combined with the wriggling pressure Dean was pushing into his ass made his heart skip a beat.

Dean sensed that Cas was on edge and moved his tongue more quickly over Cas’s head. He pumped his lips harder and teased Cas’s hole with a single finger, combining the three sensations in a trifecta of pleasure for the angel. Cas’s breathing became more ragged, coming in quick pants and moans. “Dean… Dean…” came the angel’s voice in quiet breaths.

Dean moaned around Cas’s shaft, encouraging the angel, pushing him closer to the edge. After a few solid pumps, Dean decided he was ready to be done here. He angled his finger up and forward, pressing it into Cas’s most sensitive spot, while shoving his lips hard down to the base of Cas’s cock. The sensation against Cas’s prostate was all it took.

Cas felt his knees weaken and the wave of heat boiling in his torso spilled over, shooting out of him into Dean’s throat. Cas let out a deep moan, closer to a shout than anything, chest heaving and lips falling slack with Dean’s name. His eyes rolled back in his head briefly and he exhaled loudly, fighting against the leather around his wrists. All he wanted to do was grab Dean’s sandy hair and hold him there a minute longer, but Dean was already pulling back.

Cas lolled his head down and to the side to look at the demon. For a minute Cas was struck by the black eyes. In his mind, he had been picturing a green-eyed Dean, _his_ Dean. The quick reminder that this wasn’t exactly Dean Winchester dampened the moment for Cas, but not entirely. His head was still hazy with orgasm and he didn’t have time to process  the thought completely.

Dean leaned back on his knees and stood, wiping spit and Cas from his lips with the back of his wrist. He looked into the angel’s eyes, a hint of smugness there, and winked. Cas’s breathing was returning to normal and he relaxed as he Dean stepped behind him, loosening the leather around his wrists. Cas felt a little flare of shame as his hands sprung free.

It was a small, nagging chip in his conscience. What he had just done was wrong- to let a demon pervert him like that. He had been thinking to himself how wrong it was almost the whole time, but it hadn’t actually felt that way. It hadn’t felt as wrong as it should have. It wasn’t just any demon;  it was Dean, the hunter he had cared about for so long and the one he had come here to rescue. Sure, it was a corrupted version of him, but it was still Dean in there somewhere… Cas ignored his guilt, pushing it deeper into his mind. It had already happened so there was no use rehashing his inner turmoil. He resolved to hide his shame, from both the demon and himself.

Dean put a stop to Cas’s thoughts. “See what you’ve been missing?” he teased in a low voice, still behind Cas. Cas didn’t know how to answer so he remained silent, nursing his bruised wrists. To keep the guilt at bay, he decided to focus on the pleasure of the past fifteen minutes. He replayed them over and over again; Dean’s lips over his head, a tongue across his dick, a finger pressed to the right spot… Cas blushed.

“Too good for words then?” Dean gave Cas a little punch on the back of the shoulder, just a bit too hard to be entirely playful.

Cas’s thoughts abruptly flashed back to the scissors and he knew he should answer. “Yes,” he started hesitantly. Dean swung back around so that he was facing the demon, cold eyes catching the faint light of the dungeon.

“And?” Dean urged impatiently. Dean didn’t need approval that he’d done a good job. He knew that, but he wanted the angel to admit how shameful he felt, how wrong that had been… That was demon Dean’s sick fuel- others’ pain and shame and humiliation. He knew the innocent angel’s shame would be particularly sweet. But he never got it.

Cas didn’t know what to do now. He knew he was still at the demon’s mercy so he decided it might be best to keep Dean talking.  “I am just thinking, Dean. What will this mean when we return?” Cas tried to keep his voice even, to hide his doubts about what had just happened.

 “What will this _mean_?” Dean asked incredulously. His jaw fell slack in angry disappointment. He stared into Cas’s eyes, searching them for a hint of shame or self-revulsion. There was nothing. Cas stared back at Dean, curious but resolute, awaiting a response. The inquisitive look in Castiel’s eyes infuriated Dean. He snarled and looked away from the angel.

This was not the reaction he wanted. He wanted the angel to be disgusted with himself, to reel back in horror at what he had done, to be sick that he had done something so twisted and _liked_ it. That was what Dean needed to see in Castiel’s eyes, but instead he was met with calm. He wanted shame and guilt and pain and humiliation to be written clearly across the angel’s face.

He **would** get that, however he had to.

He whipped his body around and brought his intimidating figure within inches of the angel, raven eyes burnishing. With bared teeth and a husky growl, Dean leaned in to Castiel’s face.

“Who says we’re done here?”

**Notes for the Chapter:**

> I had a lot of trouble working this chapter out to convey exactly what I wanted. I am not exactly in love with how it turned out, but I think I got it across.
> 
> What I wanted to show was a Castiel that was reluctant to give in because of the obvious taboo- he's an angel, this is a demon, and more importantly, it's his friend.  
> I wanted him to resist it until he really couldn't stand it anymore and then convince himself it wasn't that bad because it was still technically Dean and he actually cared about Dean. That wasn't too terribly difficult to write.
> 
> Dean, on the other hand, was a nightmare! It took a lot of effort to create a sadistic and twisted Dean that was still interested in Cas's feelings. I wanted him right on that line, where his demon nature needed to hurt Castiel, but what little of human!Dean is left is taking advantage of this opportunity to see how Cas really feels. 
> 
> Basically, they are both using this situation as an excuse to get what they want. They're taking advantage of Hell's lack of moral code and the absence of Dean's humanity to explore things they don't normally get to- their feelings and their sexuality together. 
> 
> I hope I construed that in a believable way! Let me know what you guys think! Any and all opinions are welcome! Thanks again!


End file.
